As a manufacturing method of an aldehyde compound using a norbornene compound, for example, the methods described in Patent Documents 1 to 3 are known.
Patent Documents 1 to 3 disclose methods for manufacturing formyl cyan norbornane by hydroformylating cyan norbornene by using a mixed gas of H2/CO in the presence of a catalyst. Patent Documents 1 and 2 disclose an example in which a metal compound is used as a catalyst. Herein, because a target compound can be obtained with a high degree of selectivity, and a reaction pressure can be kept low, a rhodium complex is preferably used as a catalyst.
Patent Document 4 describes a metal ligand complex catalyst. In this document, rhodium is exemplified as a metal, and an organic phosphorus ligand is exemplified as a ligand.
Patent Document 5 discloses a method for treating a solution, which contains a trivalent phosphorus compound, a rhodium compound, and an aldehyde compound, that is for recovering the rhodium metal. In the document, hydrolysis using water and a base compound such as NaOH is used.